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(NHC)Copper( I )‐Catalyzed [3+2] Cycloaddition of Azides and Mono‐ or Disubstituted Alkynes
Author(s) -
DíezGonzález Silvia,
Correa Andrea,
Cavallo Luigi,
Nolan Steven P.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600961
Subject(s) - cycloaddition , catalysis , chemistry , carbene , alkyne , combinatorial chemistry , solvent , copper , click chemistry , organic chemistry , polymer chemistry
A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3‐triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N‐heterocyclic carbene). Extremely high reaction rates and excellent yields were obtained in all cases. This catalytic system fulfils the requirements of “click chemistry” with its mild and convenient conditions, notably in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper‐catalyzed cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.